Sodium bis(trimethylsilyl)amide → 348113-81-5

HRID 1992566Notes

Reaction equation

HRID 1992566 reaction equation
C(O[C:4](=[O:20])[C:5]([CH3:19])([S:14][C:15](=[O:18])[CH2:16][CH3:17])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])C.C[Si]([N-][Si](C)(C)C)(C)C.[Na+]>>[OH:20][C:4]1[C:5]([CH3:19])([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])[S:14][C:15](=[O:18])[C:16]=1[CH3:17]

Participants

3

Reactant 2

HCID 2724254Sodium bis(trimethylsilyl)amideHCID 11738193(+/-)-2-Methyl 2-propionylsulfanyl-decanoic acid ethyl ester

Product 1

HCID 135411009348113-81-5Yield 99.9%

Procedure

From 30 (469 mg, 1.55 mmol) and NaHMDS (3.87 mL, 3.87 mmol, 1.0 M in TH) following general procedure G was obtained 34 (397 mg, 70%). 1H NMR (300 MHz, CDCl3) (enol tautomer) δ 0.86 (t, J=6.8 Hz, 3H), 1.23 (s, 11H), 1.30-1.45 (m, 1H), 1.59 (s, 3H), 1.74 (s, 3H), 1.84-1.88 (m, 2H); 13C NMR (75 MHz, CDCl3) δ 7.48, 14.0, 22.6, 25.2, 25.9, 29.2, 29.4, 29.6, 31.8, 38.5, 58.2, 110.5, 180.9, 198.0. IR (NaCl) 2927, 1601 cm−1

Sources & evidence

ORD record
ord-0ffd62f12eac4285b898f8ca7837859f
Source dataset
uspto-grants-2010_01
Patent number
US07649012B2

Reaction notes

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